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Phenyl thioxochloroformate → (R)-2,2-dimethyl-4-(1-methyl-1-phenoxythiocarbonyloxy-2-phenyl-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1911522
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1911522
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([OH:22])([CH3:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:24])[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li].C[Si]([N-][Si](C)(C)C)(C)C.[CH:35]1[CH:40]=[CH:39][C:38]([O:41][C:42](Cl)=[S:43])=[CH:37][CH:36]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([CH3:21])([O:22][C:42]([O:41][C:38]2[CH:39]=[CH:40][CH:35]=[CH:36][CH:37]=2)=[S:43])[CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:24])[CH3:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 70498Phenyl thioxochloroformateHCID 68714982HCID 68714982, VerbindungHCID 86605622Lithium bistrimethylsilylamide

Produkt 1

HCID 86623840(R)-2,2-dimethyl-4-(1-methyl-1-phenoxythiocarbonyloxy-2-phenyl-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

A stirred solution of (R)-4-(1-hydroxy-1-methyl-2-phenyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.50 g) in THF (25 ml) was cooled under an argon atmosphere to −78° C. and treated dropwise with 1 M lithium-bis-(trimethylsilyl)amide in THF (1.79 ml). The solution was allowed to warm to r.t. Then, phenyl chlorothionoformate (0.3 ml) was added. After stirring at r.t. for 2 hrs, the reaction mixture was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated to give crude (R)-2,2-dimethyl-4-(1-methyl-1-phenoxythiocarbonyloxy-2-phenyl-ethyl)-oxazoli-dine-3-carboxylic acid tert-butyl ester as pale yellow oil which was used in the next reaction step without further purification.

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5cbaa224745c43ecb4a48890e26a307e
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08604061B2

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